NCBI Taxonomy: 5592
Microascales (ncbi_taxid: 5592)
found 358 associated metabolites at order taxonomy rank level.
Ancestor: Hypocreomycetidae
Child Taxonomies: Microascaceae, Graphiaceae, Halosphaeriaceae, Ceratocystidaceae, Gondwanamycetaceae, Chadefaudiellaceae, environmental samples, unclassified Microascales, Microascales incertae sedis
Scopoletin
Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).
Umbelliferone
Umbelliferone is a hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7. It has a role as a fluorescent probe, a plant metabolite and a food component. Umbelliferone is a natural product found in Ficus septica, Artemisia ordosica, and other organisms with data available. See also: Chamomile (part of). Occurs widely in plants including Angelica subspecies Phytoalexin of infected sweet potato. Umbelliferone is found in many foods, some of which are macadamia nut, silver linden, quince, and capers. Umbelliferone is found in anise. Umbelliferone occurs widely in plants including Angelica species Phytoalexin of infected sweet potat A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7. [Raw Data] CB220_Umbelliferone_pos_50eV_CB000077.txt [Raw Data] CB220_Umbelliferone_pos_40eV_CB000077.txt [Raw Data] CB220_Umbelliferone_pos_30eV_CB000077.txt [Raw Data] CB220_Umbelliferone_pos_10eV_CB000077.txt [Raw Data] CB220_Umbelliferone_pos_20eV_CB000077.txt [Raw Data] CB220_Umbelliferone_neg_40eV_000039.txt [Raw Data] CB220_Umbelliferone_neg_10eV_000039.txt [Raw Data] CB220_Umbelliferone_neg_30eV_000039.txt [Raw Data] CB220_Umbelliferone_neg_20eV_000039.txt Umbelliferone. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=93-35-6 (retrieved 2024-07-12) (CAS RN: 93-35-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent. Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent.
Lovastatin
Lovastatin is a fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). It has a role as an Aspergillus metabolite, a prodrug, an anticholesteremic drug and an antineoplastic agent. It is a polyketide, a statin (naturally occurring), a member of hexahydronaphthalenes, a delta-lactone and a fatty acid ester. It is functionally related to a (S)-2-methylbutyric acid and a mevastatin. Lovastatin, also known as the brand name product Mevacor, is a lipid-lowering drug and fungal metabolite derived synthetically from a fermentation product of Aspergillus terreus. Originally named Mevinolin, lovastatin belongs to the statin class of medications, which are used to lower the risk of cardiovascular disease and manage abnormal lipid levels by inhibiting the endogenous production of cholesterol in the liver. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase, which catalyzes the conversion of HMG-CoA to mevalonic acid and is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America. Lovastatin and other drugs from the statin class of medications including [atorvastatin], [pravastatin], [rosuvastatin], [fluvastatin], and [simvastatin] are considered first-line options for the treatment of dyslipidemia. Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world. Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD. Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality. Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack. Evidence has shown that even for low-risk individuals (with <10\\\\% risk of a major vascular event occurring within 5 years) statins cause a 20\\\\%-22\\\\% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks. While all statin medications are considered equally effective from a clinical standpoint, [rosuvastatin] is considered the most potent; doses of 10 to 40mg [rosuvastatin] per day were found in clinical studies to result in a 45.8\\\\% to 54.6\\\\% decrease in LDL cholesterol levels, while lovastatin has been found to have an average decrease in LDL-C of 25-40\\\\%. Potency is thought to correlate to tissue permeability as the more lipophilic statins such as lovastatin are thought to enter endothelial cells by passive diffusion, as opposed to hydrophilic statins such as [pravastatin] and [rosuvastatin] which are taken up into hepatocytes through OATP1B1 (org... Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6 position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today. A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor D009676 - Noxae > D000963 - Antimetabolites CONFIDENCE standard compound; EAWAG_UCHEM_ID 3139 CONFIDENCE standard compound; INTERNAL_ID 2212 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.
Hypericin
Hypericin is found in alcoholic beverages. Hypericin is widespread in Hypericum species especially Hypericum perforatum (St Johns Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint Johns wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine -hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents Widespread in Hypericum subspecies especies Hypericum perforatum (St Johns Wort) D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D011838 - Radiation-Sensitizing Agents D000970 - Antineoplastic Agents C1907 - Drug, Natural Product D004791 - Enzyme Inhibitors Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene. Hypericin is a natural product found in Hypericum adenotrichum, Hypericum bithynicum, and other organisms with data available. Hypericin is an anthraquinone derivative that is naturally found in the yellow flower of Hypericum perforatum (St. Johns wort) with antidepressant, potential antiviral, antineoplastic and immunostimulating activities. Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, gamma-amino butyric acid (GABA) and L-glutamate, which may contribute to its antidepressant effect. Hypericin may also prevent the replication of encapsulated viruses probably due to inhibition of the assembly and shedding of virus particles in infected cells. This agent also exerts potent phototoxic effects by triggering apoptotic signaling that results in formation of reactive oxygen species. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3]. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3].
4-Hydroxybenzaldehyde
4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor. 4-Hydroxybenzaldehyde is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-08-0 (retrieved 2024-07-02) (CAS RN: 123-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.
Succinic acid
Succinic acid appears as white crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste. (NTP, 1992) Succinic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. It has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. It is an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid. It is a conjugate acid of a succinate(1-). A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity. Succinate is commonly used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Succinate plays a role in the citric acid cycle, an energy-yielding process and is metabolized by succinate dehydrogenase to fumarate. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e.g. malate. (A3509) Mutations in the four genes encoding the subunits of succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (A3510). Succinate also acts as an oncometabolite. Succinate inhibits 2-oxoglutarate-dependent histone and DNA demethylase enzymes, resulting in epigenetic silencing that affects neuroendocrine differentiation. A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid (succinate) is a dicarboxylic acid. It is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate is found in all living organisms ranging from bacteria to plants to mammals. In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA). Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate (PMID 16143825). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space. Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule. Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or it can exhibit hormone-like signaling functions (PMID: 26971832). As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP. Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome. Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. In humans, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid is widely distributed in higher plants and produced by microorganisms. It is found in cheeses and fresh meats. Succinic acid is a flavouring enhancer, pH control agent [DFC]. Succinic acid is also found in yellow wax bean, swamp cabbage, peanut, and abalone. An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID S004 Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].
Tyrosol
Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285). 2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent, a fungal metabolite, a geroprotector and a plant metabolite. It is functionally related to a 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol is a natural product found in Thalictrum petaloideum, Casearia sylvestris, and other organisms with data available. Tyrosol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents A phenol substituted at position 4 by a 2-hydroxyethyl group. D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].
Palmitic acid
Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Ergosterol
Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.
4-hydroxyphenylacetate
p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic. p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate. p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain. 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate. 4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available. 4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Constituent of sweet clover (Melilotus officinalis) and yeast Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].
L-3-Phenyllactic acid
L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. [HMDB] L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. (±)-3-Phenyllactic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=828-01-3 (retrieved 2024-07-04) (CAS RN: 828-01-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (S)-2-Hydroxy-3-phenylpropanoic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria. D-?(+)?-?Phenyllactic acid is an anti-bacterial agent, excreted by Geotrichum candidum, inhibits a range of Gram-positive from humans and foodstuffs and Gram-negative bacteria found in humans[1]. DL-3-Phenyllactic acid is a broad-spectrum antimicrobial compound. DL-3-Phenyllactic acid is a broad-spectrum antimicrobial compound.
Emodin
Emodin appears as orange needles or powder. (NTP, 1992) Emodin is a trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs. It has a role as a tyrosine kinase inhibitor, an antineoplastic agent, a laxative and a plant metabolite. It is functionally related to an emodin anthrone. It is a conjugate acid of an emodin(1-). Emodin has been investigated for the treatment of Polycystic Kidney. Emodin is a natural product found in Rumex dentatus, Rhamnus davurica, and other organisms with data available. Emodin is found in dock. Emodin is present in Cascara sagrada.Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. (Wikipedia) Emodin has been shown to exhibit anti-inflammatory, signalling, antibiotic, muscle building and anti-angiogenic functions (A3049, A7853, A7854, A7855, A7857). Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies. See also: Reynoutria multiflora root (part of); Frangula purshiana Bark (part of). A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs. Emodin is found in dock. Emodin is present in Cascara sagrada.Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. (Wikipedia C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D005765 - Gastrointestinal Agents > D002400 - Cathartics Present in Cascara sagrada CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 ORIGINAL_PRECURSOR_SCAN_NO 5094; CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 [Raw Data] CB029_Emodin_pos_50eV_CB000015.txt [Raw Data] CB029_Emodin_pos_10eV_CB000015.txt [Raw Data] CB029_Emodin_pos_20eV_CB000015.txt [Raw Data] CB029_Emodin_pos_30eV_CB000015.txt [Raw Data] CB029_Emodin_pos_40eV_CB000015.txt [Raw Data] CB029_Emodin_neg_50eV_000008.txt [Raw Data] CB029_Emodin_neg_20eV_000008.txt [Raw Data] CB029_Emodin_neg_40eV_000008.txt [Raw Data] CB029_Emodin_neg_30eV_000008.txt [Raw Data] CB029_Emodin_neg_10eV_000008.txt CONFIDENCE standard compound; ML_ID 38 Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3]. Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3].
3-(4-hydroxyphenyl)lactate
Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416). Acquisition and generation of the data is financially supported in part by CREST/JST. Hydroxyphenyllactic acid is an antifungal metabolite.
Patulin
Patulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins D009676 - Noxae > D009153 - Mutagens Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].
Enniatin B
An enniatin obtained from formal cyclocondensation of three N-[(2R)-2-hydroxy-3-methylbutanoyl]-N-methyl-L-valine units. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents CONFIDENCE Reference Standard (Level 1)
Questin
Questin is an antibacterial agent isolated from marine Aspergillus flavipes. Questin exhibits antibacterial activity against V. harveyi, V. anguillarum, V. cholerae, and V. parahemolyticus with MIC values of 31.25 μg/mL, 62.5 μg/mL, 62.5 μg/mL, and 125 μg/mL[1]. Questin is an antibacterial agent isolated from marine Aspergillus flavipes. Questin exhibits antibacterial activity against V. harveyi, V. anguillarum, V. cholerae, and V. parahemolyticus with MIC values of 31.25 μg/mL, 62.5 μg/mL, 62.5 μg/mL, and 125 μg/mL[1].
Gliotoxin
Gliotoxin is a pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. It has a role as a mycotoxin, an immunosuppressive agent, an EC 2.5.1.58 (protein farnesyltransferase) inhibitor, a proteasome inhibitor and an antifungal agent. It is an organic disulfide, a pyrazinoindole, an organic heterotetracyclic compound and a dipeptide. Gliotoxin is a natural product found in Streptomyces, Aspergillus cejpii, and other organisms with data available. Gliotoxin is a sulfur-containing antibiotic produced by several species of fungi, some of which are pathogens of humans such as Aspergillus, and also by species of Trichoderma, and Penicillium. Gliotoxin possesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, granulocytes, macrophages, and thymocytes. (L1941) A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent. A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring; mycotoxin produced by several species of fungi. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins C308 - Immunotherapeutic Agent > C574 - Immunosuppressant
(-)-Dihydrocarveol
p-Menth-8-en-2-ol is found in herbs and spices. p-Menth-8-en-2-ol occurs in Mentha species, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredien Occurs in Mentha subspecies, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredient. p-Menth-8-en-2-ol is found in herbs and spices.
Citronellyl acetate
Citronellyl acetate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1]. Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1].
(-)-Isopulegol
Isolated from Mentha pulegium (European pennyroyal) and other essential oils. (-)-Isopulegol is found in many foods, some of which are lemon balm, lemon grass, rosemary, and fats and oils. (-)-Isopulegol is found in cornmint. (-)-Isopulegol is isolated from Mentha pulegium (European pennyroyal) and other essential oil
Cladosporin
D004791 - Enzyme Inhibitors
Enniatin B
Gliotoxin
Dihydroisocarveol
(-)-dihydrocarveol, also known as (1r,2r,5r)-5-isopropenyl-2-methylcyclohexanol or (1r,2r,4r)-P-menth-8-en-2-ol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (-)-dihydrocarveol is considered to be an isoprenoid lipid molecule (-)-dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-dihydrocarveol can be found in fats and oils and herbs and spices, which makes (-)-dihydrocarveol a potential biomarker for the consumption of these food products.
Hydroxyphenyllactic acid
Hydroxyphenyllactic acid is an antifungal metabolite.
PHENYLACETIC ACID
D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents
Palmitic Acid
COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
4-Hydroxyphenylacetic acid
4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].
6-METHYL-5-HEPTEN-2-ONE
Sulcatone is an endogenous metabolite. Sulcatone is an endogenous metabolite.
(-)-Dihydrocarveol
p-Menth-8-en-2-ol is found in herbs and spices. p-Menth-8-en-2-ol occurs in Mentha species, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredien Occurs in Mentha subspecies, Piper longum (long pepper), Heracleum candicans and other essential oils. Stereoisomeric mixture used as flavour ingredient. p-Menth-8-en-2-ol is found in herbs and spices.
Hypericin
Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene. Hypericin is a natural product found in Hypericum adenotrichum, Hypericum bithynicum, and other organisms with data available. Hypericin is an anthraquinone derivative that is naturally found in the yellow flower of Hypericum perforatum (St. Johns wort) with antidepressant, potential antiviral, antineoplastic and immunostimulating activities. Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, gamma-amino butyric acid (GABA) and L-glutamate, which may contribute to its antidepressant effect. Hypericin may also prevent the replication of encapsulated viruses probably due to inhibition of the assembly and shedding of virus particles in infected cells. This agent also exerts potent phototoxic effects by triggering apoptotic signaling that results in formation of reactive oxygen species. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D011838 - Radiation-Sensitizing Agents D000970 - Antineoplastic Agents C1907 - Drug, Natural Product D004791 - Enzyme Inhibitors Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3]. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3].
Scopoletin
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).
Ergosterol
Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.
Emodin
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D005765 - Gastrointestinal Agents > D002400 - Cathartics CONFIDENCE isolated standard relative retention time with respect to 9-anthracene Carboxylic Acid is 1.288 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.291 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.286 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.293 Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3]. Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3].
Lovastatin
C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 2212 D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.415 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.416 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.421 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.419 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.
2,3-Dihydroxybenzoic acid
A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta. D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma, and has increased levels after aspirin ingestion. Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma, and has increased levels after aspirin ingestion.
PHENYLACETIC ACID
A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents
Succinic acid
Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].
Hydroxyphenyllactic acid
Hydroxyphenyllactic acid is a tyrosine metabolite. It is carcinogenic. The level of hydroxyphenyllactic acid is elevated in patients with deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2). (PMID 4720815) [HMDB] Hydroxyphenyllactic acid is an antifungal metabolite.
Umbelliferone
Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent. Umbelliferone (7-Hydroxycoumarin), a natural product of the coumarin family, is a fluorescing compound which can be used as a sunscreen agent.
2,3,6,8-tetrahydroxy-1-methylxanthen-9-one
3-hydroxy-4-(2,6,7-trihydroxy-6-methylheptan-2-yl)benzoic acid
p-Hydroxybenzaldehyde
p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.
2-Pyrocatechuic acid
Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma, and has increased levels after aspirin ingestion. Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma, and has increased levels after aspirin ingestion.
L-3-Phenyllactic acid
(S)-2-Hydroxy-3-phenylpropanoic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria.
4-Hydroxybenzaldehyde
p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.
patulin
D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE standard compound; INTERNAL_ID 5971 D009676 - Noxae > D009153 - Mutagens CONFIDENCE Reference Standard (Level 1) Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].
Dormin
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D006133 - Growth Substances > D010937 - Plant Growth Regulators (±)-Abscisic acid is an orally active plant hormone that is present also in animals. (±)-Abscisic acid (ABA) contributes to the regulation of glycemia in mammals[1]. (±)-Abscisic acid is an orally active plant hormone that is present also in animals. (±)-Abscisic acid (ABA) contributes to the regulation of glycemia in mammals[1]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2].
Citronellyl acetate
Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1]. Citronellyl acetate is a monoterpene product of the secondary metabolism of plants, with antinociceptive activity. Citronellyl acetate exhibits pro-apoptotic activity in human hepatoma cells. Citronellyl acetate shows fungicidal, larvicidal, bactericidal and repelling/insecticidal effects[1].
Isopulegol
A natural product found in Citrus hystrix.
Tyrosol
Tyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosols SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart . D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].
3-Hydroxy-4-(2,6,7-trihydroxy-6-methylheptan-2-yl)benzoic acid
5-Hydroxymethyl-2-furoic acid
A member of the class of furoic acids that is 2-furoic acid substituted at position 5 by a hydroxymethyl group. 5-(Hydroxymethyl)-2-furancarboxylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=6338-41-6 (retrieved 2024-07-16) (CAS RN: 6338-41-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally. 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.
3,6,12,18-tetraisopropyl-4,10,16-trimethyl-9,15-bis(2-methylpropyl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
(4r)-4-{[(3s)-2,3-dihydroxyindol-3-yl]methyl}-1-(propan-2-ylidene)-2h,3h,4h-pyrazino[2,1-b]quinazolin-6-one
6-[(2r)-4-hydroxypentan-2-yl]-4-methoxy-3-methylpyran-2-one
(2r,3r)-2-[(2s,4r)-7-hydroxy-4-methyl-6-methylideneoctan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
2-{[1-hydroxy-2,2-bis(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)-n-methyl-3-oxopropanimidic acid
2-(6-hydroxy-4,6-dimethyloct-7-en-2-yl)-6-oxo-2,3-dihydropyran-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
4-[(3e)-4,8-dimethyl-6-oxonona-3,7-dien-1-yl]-5h-furan-2-one
(1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(2r,3r)-2-[(2s,4r,6e)-4,6-dimethyloct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
16-[(3-hydroxyoctanoyl)oxy]-2,13-dioxo-8,19-dioxa-23,24,25,26-tetrathia-3,14-diazahexacyclo[10.10.4.0¹,¹⁴.0³,¹².0⁴,¹⁰.0¹⁵,²¹]hexacosa-6,9,17,20-tetraen-5-yl 3-hydroxyoctanoate
15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl 3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O8S2 (630.2069468000001)
(2s,7s)-2-{[(1s)-1-{[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}ethyl]amino}-7-hydroxy-4-oxooctanoic acid
(2s,3s)-n-[(3s,6s,12s,15r,20as)-15-benzyl-3,6-bis[(2s)-butan-2-yl]-1,4,7,13-tetrahydroxy-16-oxo-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-3-methyl-2-(n-methylacetamido)pentanimidic acid
C40H63N7O7 (753.4788728000001)
2-[5-(2,3-dimethyloxiran-2-yl)-4-methylpentan-2-yl]-6-oxo-2,3-dihydropyran-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(4e)-5-[(1s)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
4-[(2s,3r,8r,10r)-2-(dimethylamino)-3-hydroxy-8,10-dimethyldodec-6-en-1-yl]phenol
n-(3,6-dihydroxyhexan-2-yl)-3-[2-(dodecan-2-yl)-3,4,7,10,13-pentahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(hydroxymethyl)-17-oxo-15-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-4,7,10,13-tetraen-9-yl]propanimidic acid
C43H70N6O12 (862.5051460000001)
(1r,2s,4r,5r,8r,9s,11s)-9-formyl-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-6-(hydroxymethyl)-5-methoxy-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
4,5,14-trihydroxy-15-(hydroxymethyl)-4,7,12-trimethyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),7,11,13-tetraene-6,10-dione
3,4-dihydroxy-7-methyl-2-(prop-1-en-1-yl)-hexahydro-2h-pyrano[3,2-c]pyran-5-one
5-ethyl-4-hydroxy-3-methoxy-5-methyl-2-(sec-butyl)cyclopent-2-en-1-one
(3r)-6-hydroxy-3-(4-hydroxy-4-methylpentyl)-3-methyl-2-benzofuran-1-one
15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl 3-hydroxyoctanoate
C28H36N2O7S2 (576.1963826000001)
6-hydroxy-3-methyl-3-(4-methylpentyl)-2-benzofuran-1-one
(5s)-5-[(7s,8e)-7-hydroxytetradec-8-en-1-yl]oxolan-2-one
2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-4-en-2-yl)hexadecanimidic acid
(2r,2's,3r,3'as,6'as)-2'-methyl-6'-methylidene-3-(2-methylprop-1-en-1-yl)-tetrahydro-2'h-spiro[oxirane-2,1'-pentalen]-4'-one
2-{[(4-butanoyl-3-methoxy-5-methylphenyl)(hydroxy)methylidene]amino}-3-hydroxypropanoic acid
C16H21NO6 (323.13688060000004)
(2r,3r)-2-[(2s,4r,6s)-6-hydroxy-4,6-dimethyloct-7-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(3r)-3,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one
n-[(4s,5r,7s,9s)-7-ethyl-9-hydroxy-8,8-dimethyl-2-oxo-1,6-dioxaspiro[4.5]decan-4-yl]ethanimidic acid
(2s,9s,9ar)-2-ethyl-9-hydroxy-9-{[(4r)-3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-1h,2h,9ah-imidazo[1,2-a]indol-3-one
C27H27N5O4 (485.20629420000006)
n-(3,6-dihydroxyhexan-2-yl)-3-[2-(dodec-10-en-2-yl)-3,4,7,10,13-pentahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(hydroxymethyl)-17-oxo-15-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-4,7,10,13-tetraen-9-yl]propanimidic acid
C43H68N6O12 (860.4894968000001)
3,4,6,8-tetrahydroxy-3-methyl-4h-2-benzopyran-1-one
(3s,6s)-3-methyl-6-{[5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol
n-[15-benzyl-1,4,7,13-tetrahydroxy-6-isopropyl-16-oxo-3-(sec-butyl)-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylbutanimidic acid
(3s,6s,9r,12s,19s)-3-benzyl-19-(hexan-2-yl)-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C34H53N5O7 (643.3944787999999)
2-(4,6-dimethyloct-6-en-2-yl)-6-oxo-2,3-dihydropyran-3-yl 6-[(acetyloxy)methyl]-8-hydroxy-4-methylocta-2,4-dienoate
16-[(3-hydroxyoctanoyl)oxy]-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl 3-hydroxyoctanoate
C36H50N2O10S2 (734.2906720000001)
n-[15-benzyl-1,4,7,13-tetrahydroxy-16-oxo-3,6-bis(sec-butyl)-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylbutanimidic acid
C38H59N7O7 (725.4475744000001)
n-[15-benzyl-1,4,7,13-tetrahydroxy-6-isopropyl-16-oxo-3-(sec-butyl)-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylpentanimidic acid
C38H59N7O7 (725.4475744000001)
(2r)-2-hydroxy-1-[(1s,5s,6s)-1-hydroxy-6-methyl-4-methylidenebicyclo[3.2.0]heptan-6-yl]-4-methylpent-3-en-1-one
1-[5,6-dihydroxy-1,8-dimethyl-2-(sec-butyl)-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]-3-hydroxypropan-1-one
5-(chloromethyl)-5-hydroxy-6-(hydroxymethyl)-6-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]oxan-2-one
(2r,3r)-2-[(2s,4r)-5-(2,3-dimethyloxiran-2-yl)-4-methylpentan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(2r,3r)-2-[(2s,4r)-5-[(2s,3s)-2,3-dimethyloxiran-2-yl]-4-methylpentan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
3-[17-(dodecan-2-yl)-6,9,12,15,16-pentahydroxy-13-(hydroxymethyl)-10-(1h-indol-3-ylmethyl)-2-oxo-4-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-5,8,11,14-tetraen-7-yl]propanimidic acid
C43H60N6O9 (804.4421550000001)
(3r)-6-hydroxy-8-methoxy-3-{[(2r,6s)-6-methyloxan-2-yl]methyl}-3,4-dihydro-2-benzopyran-1-one
3-heptyl-3,9-dihydroxy-7,8-dimethoxy-1h,4h-naphtho[2,3-c]pyran-5,10-dione
5-hydroxy-9-[3-(5-hydroxy-6,14-dimethyl-2,8,11-trioxo-1,7-dioxacyclotetradec-3-en-9-yl)-6-methyl-2,4-dioxooxan-3-yl]-6,14-dimethyl-1,7-dioxacyclotetradec-3-ene-2,8,11-trione
(2r)-2-{[1-hydroxy-2,2-bis(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)-n-methyl-3-oxopropanimidic acid
n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid
C26H51NO3 (425.38687360000006)
4-(4,8-dimethyl-6-oxonona-3,7-dien-1-yl)-5h-furan-2-one
2-(4,6-dimethyloct-6-en-2-yl)-6-oxo-2,3-dihydropyran-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
n-[15-benzyl-1,4,7,13-tetrahydroxy-16-oxo-3,6-bis(sec-butyl)-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-3-methyl-2-(n-methylacetamido)pentanimidic acid
C40H63N7O7 (753.4788728000001)
4-hydroxy-3,9,13-trimethyl-3,4,9,10,11,12a,16,16a-octahydro-2,8-benzodioxacyclotetradecine-1,7,12,15-tetrone
3,6,9-trihydroxy-8-methoxy-3-methyl-2,4-dihydroanthracen-1-one
(2r,3r)-2-[(2s,4r,6z)-4,6-dimethyl-8-oxooct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(4r,5s)-2-[(2s)-butan-2-yl]-5-ethyl-4-hydroxy-3-methoxy-5-methylcyclopent-2-en-1-one
(2r,3r)-2-[(2s,4r,6r)-6-hydroxy-4,6-dimethyloct-7-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
3-benzyl-19-(decan-2-yl)-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
(5s,7r)-3-{[(2s,3r,8r,10r)-3-hydroxy-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-2-yl](methyl)amino}-7-[(2r)-7-methyl-3-oxooct-6-en-2-yl]-8-methylidene-1-oxaspiro[4.5]dec-3-en-2-one
(2r,3r)-2-[(2s,4r)-6-hydroxy-4,6-dimethyloct-7-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(3s,6s,9r,12s,19s)-3-benzyl-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-19-[(2s)-octan-2-yl]-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C36H57N5O7 (671.4257772000001)
(9r,9as)-9-hydroxy-9-{[(1s,4r)-3-hydroxy-1-isopropyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2,2-dimethyl-1h,9ah-imidazo[1,2-a]indol-3-one
C27H29N5O4 (487.22194340000004)
1-[(1s,2s,4ar,5s,6r,8r,8as)-2-[(2r)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]-3-hydroxypropan-1-one
(2s,9s,9ar)-9-hydroxy-9-{[(1s,4r)-3-hydroxy-1-isopropyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-isopropyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one
6-[2-(4-hydroxy-1,3-dimethylcyclohexyl)ethenyl]-3-methoxy-4-phenyl-3h-quinoline-2,4,5-triol
(3s,4r,4ar,5r,6r,8ar)-4,4a,6,8a-tetrahydroxy-5-methoxy-4-methyl-3-(3-methylbut-2-en-1-yl)-hexahydro-2-benzothiopyran-2-ium-2-olate
C16H28O6S (348.16065080000004)
3-hydroxy-4-(2-methyl-5-oxooxolan-2-yl)benzoic acid
(3s,6s,9r,12s,19s)-3-benzyl-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-19-(octan-2-yl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C36H57N5O7 (671.4257772000001)
(4s,8s)-1-(furan-3-yl)-4,9-dihydroxy-4,8-dimethylnonane-1,6-dione
(6e)-2-(dimethylamino)-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-3-one
1-(furan-3-yl)-4,8-dimethylnona-4,7-diene-1,6-dione
(3r,4r,5s)-4,5,14-trihydroxy-15-(hydroxymethyl)-4,7,12-trimethyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),7,11,13-tetraene-6,10-dione
(1r,3s,4s,5r)-4-methyl-6-methylidene-4-[(2s,3s)-3-(2-methylprop-1-en-1-yl)oxiran-2-yl]-2-oxatricyclo[3.3.0.0¹,³]octane
(2s,9s,9ar)-9-hydroxy-9-{[(4r)-3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-isopropyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one
C28H29N5O4 (499.22194340000004)
(1s,2s,5s,6r,7e,11s,15s,16s,19s,22e,24r,25s)-6,16,24-trihydroxy-1-[(3e,5r,6s,9r,14s)-5-hydroxy-6,14-dimethyl-2,8,11-trioxo-1,7-dioxacyclotetradec-3-en-9-yl]-5,11,19,25-tetramethyl-4,10,20,26-tetraoxatricyclo[14.11.1.0²,¹⁵]octacosa-7,22-diene-3,9,14,21,27,28-hexone
(2s)-2-hydroxy-2,4-dimethyl-5-[(2s,4s,6r,8r)-4,6,8-trimethyldecan-2-yl]furan-3-one
1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
6,16,24-trihydroxy-1-(5-hydroxy-6,14-dimethyl-2,8,11-trioxo-1,7-dioxacyclotetradec-3-en-9-yl)-5,11,19,25-tetramethyl-4,10,20,26-tetraoxatricyclo[14.11.1.0²,¹⁵]octacosa-7,22-diene-3,9,14,21,27,28-hexone
(2r,3s,4r,4as,7r,8as)-3,4-dihydroxy-7-methyl-2-[(1e)-prop-1-en-1-yl]-hexahydro-2h-pyrano[3,2-c]pyran-5-one
(1s,3s,4's,5r)-1-(furan-3-yl)-4',5-dimethyl-2,8-dioxaspiro[bicyclo[3.2.1]octane-3,2'-oxolane]
5,6,14-trihydroxy-15-(hydroxymethyl)-4,7,12-trimethyl-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
(1r,6r,7s)-2,2'-dihydroxy-1,4-dimethyl-8-thia-3,4-diazaspiro[bicyclo[4.2.0]octane-7,3'-indol]-2-en-5-one
C14H13N3O3S (303.06775880000004)
[(1s,2r,3s)-1,2-dihydroxy-3-methoxy-2-[(2s,3s)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-oxocyclohexyl]methyl (2r)-2-hydroxy-3-[(1s,5s,7r)-7-methyl-2-methylidene-7-(4-methylpenta-1,3-dien-1-yl)-6-oxabicyclo[3.2.1]octan-5-yl]propanoate
2-[(1-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)amino]-7-hydroxy-4-oxooctanoic acid
3-({1-[(5-aminopentyl)-c-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl}-c-hydroxycarbonimidoyl)oxirane-2-carboxylic acid
(3s,6s,12s,18s,25s,28s,31s,34s,37s,40s,46s,49s)-15-benzyl-3,25-bis[(2s)-butan-2-yl]-5,36,48-trihydroxy-31,37-bis[(1r)-1-hydroxyethyl]-12,28,34-triisopropyl-13,26,29,32,38,46-hexamethyl-16-oxa-1,4,10,13,23,26,29,32,35,38,44,47-dodecaazapentacyclo[47.4.0.0⁶,¹⁰.0¹⁸,²³.0⁴⁰,⁴⁴]tripentaconta-4,35,47-triene-2,11,14,17,24,27,30,33,39,45-decone
3-methyl-6-{[7-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol
5-hydroxy-6,14-dimethyl-9-(2-oxopent-3-en-1-yl)-1,7-dioxacyclotetradec-3-ene-2,8,11-trione
(2r,3r)-2-[(2s,4r,6e)-4,6-dimethyloct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-6-[(acetyloxy)methyl]-8-hydroxy-4-methylocta-2,4-dienoate
(3s,6s)-3-methyl-6-{[7-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol
(2s,3s)-3-{[(1s)-1-[(5-aminopentyl)-c-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}oxirane-2-carboxylic acid
(1r,11r,14s,15s)-5-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-4,6,8,16,19-pentaen-15-yl (2r,3s,4s)-3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H36N2O8S2 (628.1912976000001)
(2r,7s)-2-{[(1r)-1-{[(1r)-1-carboxy-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}ethyl]amino}-7-hydroxy-4-oxooctanoic acid
(2s,3r)-2-[(2s,4r,6e)-4,6-dimethyloct-6-en-2-yl]-6-oxooxan-3-yl (2e,4e,6r)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
3-[(2s)-2-hydroxypropyl]-4-(5-oxohexa-1,3-dien-1-yl)-5h-furan-2-one
3-heptyl-3,5,10-trihydroxy-7-methoxy-1h,4h-naphtho[2,3-c]pyran-8,9-dione
(3e,5r,6s,9r,14s)-5-hydroxy-6,14-dimethyl-9-[(3e)-2-oxopent-3-en-1-yl]-1,7-dioxacyclotetradec-3-ene-2,8,11-trione
9-formyl-2-({[3-hydroxy-6-(hydroxymethyl)-5-methoxy-4-[(2-methylhexa-2,4-dienoyl)oxy]oxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
methyl 6-(dimethoxymethyl)-2,8-dihydroxy-9-oxoxanthene-1-carboxylate
(2s,3s)-3-{[(1s)-1-[(4-aminobutyl)-c-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}oxirane-2-carboxylic acid
(1r,4s,5s,11r,14s,15s)-15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl (3s)-3-hydroxyoctanoate
C28H36N2O7S2 (576.1963826000001)
(2r,3r)-2-[(2s,4r,6e)-4,6-dimethyl-8-oxooct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(5s)-5-[(5s,6e)-5-hydroxydodec-6-en-1-yl]oxolan-2-one
15'-hydroxy-1-methanesulfonyl-2,2,16',16'-tetramethyl-9ah-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
C28H28N4O7S (564.1678618000001)
(1r,7s,8r,11r)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0¹,⁹.0³,⁸]pentadeca-3,5-diene-10,14-dione
2,2'-dihydroxy-1,4-dimethyl-8-thia-3,4-diazaspiro[bicyclo[4.2.0]octane-7,3'-indol]-2-en-5-one
C14H13N3O3S (303.06775880000004)
[(1s,2r,3s)-1,2-dihydroxy-3-methoxy-2-[(2s,3s)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-oxocyclohexyl]methyl (2r)-2-hydroxy-3-[(1s,5s,7s)-7-methyl-2-methylidene-7-(4-methylpenta-1,3-dien-1-yl)-6-oxabicyclo[3.2.1]octan-5-yl]propanoate
(4e)-1-(furan-3-yl)-4,8-dimethylnona-4,7-diene-1,6-dione
(3s,6s,9r,12s,19s)-3-benzyl-19-[(2s)-hexan-2-yl]-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C34H53N5O7 (643.3944787999999)
(1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(1r,4s,5s,12r,15s,16s)-16-hydroxy-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl (6e)-3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O9S2 (646.2018618000001)
(1r,4s,5s,11r,14s,15s)-15-{[(3s)-3-hydroxyoctanoyl]oxy}-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl (3s)-3-hydroxyoctanoate
C36H50N2O9S2 (718.2957570000001)
(2e,6e,9r)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienoic acid
(2r,3r)-2-[(2s,4r,7r)-7-hydroxy-4-methyl-6-methylideneoctan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
4-[3-amino-8,10-dimethyl-2-(methylamino)dodec-6-en-1-yl]phenol
(1r,2s,4r,5r,8r,9s,11s)-9-formyl-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2e,4z)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
15'-hydroxy-2,2,16',16'-tetramethyl-1,9a-dihydro-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
C27H26N4O5 (486.19031060000003)
3,11-dihydroxy-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one
6-(4-hydroxypentan-2-yl)-4-methoxy-3-methylpyran-2-one
(1r,4s,5s,11r,14s,15s)-5-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-15-yl (2r,3s,4s)-3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O8S2 (630.2069468000001)
(6z)-2-ethyl-6-(hydroxymethylidene)-2-methyl-5-(sec-butyl)cyclohex-4-ene-1,3-dione
(3e)-1-[(2e)-4-hydroxy-5-pentyl-5h-1,3-oxazol-2-ylidene]-4-methylundec-3-en-2-one
9-hydroxy-9-{[3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2,2-dimethyl-1h,9ah-imidazo[1,2-a]indol-3-one
C27H27N5O4 (485.20629420000006)
methyl (1r)-1,8-dihydroxy-6-methyl-9-oxocyclopenta[b]chromene-1-carboxylate
(1r,4s,5s,12r,15s,16s)-16-{[(3s)-3-hydroxyoctanoyl]oxy}-2,13-dioxo-8,19-dioxa-23,24-dithia-3,14-diazahexacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0¹⁵,²¹]tetracosa-6,9,17,20-tetraen-5-yl (3s)-3-hydroxyoctanoate
2-hydroxy-2,4-dimethyl-5-(4,6,8-trimethyldecan-2-yl)furan-3-one
(2e,7s)-7-{[(2e,4r,5s)-4,5-dihydroxyhex-2-enoyl]oxy}-4-oxooct-2-enoic acid
(9s,9ar)-9-hydroxy-9-{[(4s)-3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2,2-dimethyl-1h,9ah-imidazo[1,2-a]indol-3-one
C27H27N5O4 (485.20629420000006)
2-ethyl-9-hydroxy-9-{[3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-1h,2h,9ah-imidazo[1,2-a]indol-3-one
C27H27N5O4 (485.20629420000006)
(5r)-5-[(1s)-1,8-dihydroxy-2,4,6-trimethyloct-6-en-1-yl]oxolan-2-one
15-[(3-hydroxyoctanoyl)oxy]-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl 3-hydroxyoctanoate
C36H50N2O9S2 (718.2957570000001)
3,4-dihydroxy-2,7-dimethyl-2-(prop-1-en-1-yl)-hexahydropyrano[3,2-c]pyran-5-one
3-[(2r,5s)-5-methyl-5-(4-methyl-2-oxopentyl)oxolan-2-yl]-5h-furan-2-one
n-[15-benzyl-1,4,7,13-tetrahydroxy-16-oxo-3,6-bis(sec-butyl)-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylpentanimidic acid
(4r,5r,8r)-9-formyl-2-({[(2r,3s,4s,5r,6r)-4-[(2e,4e)-hexa-2,4-dienoyloxy]-3-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(3s,6s,9r,12s,19s)-3-benzyl-19-(decan-2-yl)-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
2-(dimethylamino)-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-3-one
n-(3,6-dihydroxyhexan-2-yl)-3-[(6r,9s,12s,15s)-2-(dodec-10-en-2-yl)-3,4,7,10,13-pentahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(hydroxymethyl)-17-oxo-15-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-4,7,10,13-tetraen-9-yl]propanimidic acid
C43H68N6O12 (860.4894968000001)
(2s,6z)-5-[(2r)-butan-2-yl]-2-ethyl-6-{[(2-hydroxyethyl)amino]methylidene}-4-methoxy-2-methylcyclohex-4-ene-1,3-dione
5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-6,8,16,18-tetraene-2,12-dione
n-[(2s)-1-(4-methoxyphenyl)-3-oxo-4-(3,4,5-trimethoxyphenyl)butan-2-yl]carboximidic acid
(2s)-n-[(3s,6s,12s,15r,20as)-15-benzyl-3,6-bis[(2s)-butan-2-yl]-1,4,7,13-tetrahydroxy-16-oxo-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylbutanimidic acid
C38H59N7O7 (725.4475744000001)
(2s,3s)-3-hydroxy-2-methoxy-3-[(2s,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexan-1-one
3-benzyl-19-(hexan-2-yl)-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C34H53N5O7 (643.3944787999999)
2-[({3-hydroxy-5-methoxy-6-methyl-4-[(2-methylhexa-2,4-dienoyl)oxy]oxan-2-yl}oxy)methyl]-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
3-{[3-hydroxy-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-2-yl](methyl)amino}-7-(7-methyl-3-oxooct-6-en-2-yl)-8-methylidene-1-oxaspiro[4.5]dec-3-en-2-one
(2s)-2-{[(4-butanoyl-3-methoxy-5-methylphenyl)(hydroxy)methylidene]amino}-3-hydroxypropanoic acid
C16H21NO6 (323.13688060000004)
4,4a,6,8a-tetrahydroxy-5-methoxy-4-methyl-3-(3-methylbut-2-en-1-yl)-hexahydro-2-benzothiopyran-2-ium-2-olate
C16H28O6S (348.16065080000004)
2',8-dihydroxy-4,5-dimethyl-3-thia-5,7-diazaspiro[bicyclo[2.2.2]octane-2,3'-indol]-7-en-6-one
C14H13N3O3S (303.06775880000004)
(8s)-8-hydroxy-3,5,7-trimethyl-8-[(2r)-5-oxooxolan-2-yl]oct-2-enoic acid
(5-{[5-(furan-3-yl)-2-methyloxolan-2-yl]methyl}furan-3-yl)methanol
(1r,4s,5s,12r,15s,16s)-16-hydroxy-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl (3s)-3-hydroxyoctanoate
C28H36N2O8S2 (592.1912976000001)
3-methyl-6-{[5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol
16-hydroxy-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl 3-hydroxyoctanoate
C28H36N2O8S2 (592.1912976000001)
(9r,9ar)-9-hydroxy-9-{[(1s,4r)-3-hydroxy-1-isopropyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2,2-dimethyl-1h,9ah-imidazo[1,2-a]indol-3-one
C27H29N5O4 (487.22194340000004)
(9s,9as,11'r,15'r)-15'-hydroxy-1-methanesulfonyl-2,2,16',16'-tetramethyl-9ah-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
C28H28N4O7S (564.1678618000001)
(3e)-1-[(2e)-5-butyl-4-hydroxy-5h-1,3-oxazol-2-ylidene]-4-methylundec-3-en-2-one
n-(3,6-dihydroxyhexan-2-yl)-3-[(6r,9s,12s,15s)-2-(dodecan-2-yl)-3,4,7,10,13-pentahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(hydroxymethyl)-17-oxo-15-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-4,7,10,13-tetraen-9-yl]propanimidic acid
C43H70N6O12 (862.5051460000001)
{1,2-dihydroxy-3-methoxy-2-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-oxocyclohexyl}methyl 2-hydroxy-3-[7-methyl-2-methylidene-7-(4-methylpenta-1,3-dien-1-yl)-6-oxabicyclo[3.2.1]octan-5-yl]propanoate
7-[(4,5-dihydroxyhex-2-enoyl)oxy]-4-oxooct-2-enoic acid
5-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-15-yl 3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O8S2 (630.2069468000001)
9-hydroxy-9-({3-hydroxy-1-isopropyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl}methyl)-2-isopropyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one
15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-6,8,16,18-tetraen-5-yl 3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
3-hydroxy-4-[(2s)-2,6,7-trihydroxy-6-methylheptan-2-yl]benzoic acid
6-hydroxy-8-methoxy-3-[(6-methyloxan-2-yl)methyl]-3,4-dihydro-2-benzopyran-1-one
n-[4-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)-3-oxobutan-2-yl]carboximidic acid
C20H23NO5 (357.15761480000003)
n-{7-ethyl-9-hydroxy-8,8-dimethyl-2-oxo-1,6-dioxaspiro[4.5]decan-4-yl}ethanimidic acid
6-hydroxy-3-(4-hydroxy-4-methylpentyl)-3-methyl-2-benzofuran-1-one
3-hydroxy-2-methoxy-3-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexan-1-one
(1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(2s,3s,6s,8r,11s)-3,11-dihydroxy-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one
9-hydroxy-9-({3-hydroxy-1-isopropyl-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl}methyl)-2,2-dimethyl-1h,9ah-imidazo[1,2-a]indol-3-one
C27H29N5O4 (487.22194340000004)
3-benzyl-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-19-(octan-2-yl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C36H57N5O7 (671.4257772000001)
4-[(2,3-dihydroxyindol-3-yl)methyl]-1-(propan-2-ylidene)-2h,3h,4h-pyrazino[2,1-b]quinazolin-6-one
(2r,3r)-2-[(2s,4r,6e)-4,6-dimethyloct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-(acetyloxy)-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(2s,9s,9ar,11'r,15'r)-15'-hydroxy-2,16',16'-trimethyl-2,9a-dihydro-1h-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
9-hydroxy-9-{[3-hydroxy-6-oxo-1-(propan-2-ylidene)-4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-isopropyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one
C28H29N5O4 (499.22194340000004)
(3e,5r,6s,9r,14s)-5-hydroxy-9-[(6s)-3-[(3e,5r,6s,9r,14s)-5-hydroxy-6,14-dimethyl-2,8,11-trioxo-1,7-dioxacyclotetradec-3-en-9-yl]-6-methyl-2,4-dioxooxan-3-yl]-6,14-dimethyl-1,7-dioxacyclotetradec-3-ene-2,8,11-trione
2-ethyl-6-{[(2-hydroxyethyl)amino]methylidene}-4-methoxy-2-methyl-5-(sec-butyl)cyclohex-4-ene-1,3-dione
(3r,4r,7r)-8-formyl-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-12-isopropyl-4-methyltetracyclo[6.4.0.0²,¹⁰.0³,⁷]dodec-11-ene-1-carboxylic acid
(2s,9s,9ar,11's,15's)-15'-hydroxy-2,16',16'-trimethyl-2,9a-dihydro-1h-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
(3s,6s,9r,12s,19s)-3-benzyl-19-[(2s)-decan-2-yl]-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
(1r,4s,5s,11r,14s,15s)-15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-6,8,16,19-tetraen-5-yl (6e)-3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O8S2 (630.2069468000001)
(1r,4s,5s,12r,15s,16s)-16-{[(3s)-3-hydroxyoctanoyl]oxy}-2,13-dioxo-8,19-dioxa-23,24,25,26-tetrathia-3,14-diazahexacyclo[10.10.4.0¹,¹⁴.0³,¹².0⁴,¹⁰.0¹⁵,²¹]hexacosa-6,9,17,20-tetraen-5-yl (3s)-3-hydroxyoctanoate
(2s,3r)-2-[(2r,4s,6e)-4,6-dimethyloct-6-en-2-yl]-6-oxooxan-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(4r,5r,8r)-9-formyl-2-({[(2r,3s,4s,5r,6r)-4-[(2z,4e)-hexa-2,4-dienoyloxy]-3-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(3s,6s,9r,12s,19s)-3-benzyl-5,8,11,14,17-pentahydroxy-12-isopropyl-6-methyl-9-(2-methylpropyl)-19-[(2r)-octan-2-yl]-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-2-one
C36H57N5O7 (671.4257772000001)
(3r,4s)-3,4,6,8-tetrahydroxy-3-methyl-4h-2-benzopyran-1-one
1,4,7-trihydroxy-5-methoxy-2-methylanthracene-9,10-dione
(1r,4s,5s,12r,15s,16s)-16-{[(3s)-3-hydroxyoctanoyl]oxy}-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl (3s)-3-hydroxyoctanoate
C36H50N2O10S2 (734.2906720000001)
16-hydroxy-1,12-bis(methylsulfanyl)-2,13-dioxo-8,19-dioxa-3,14-diazapentacyclo[12.8.0.0³,¹².0⁴,¹⁰.0¹⁵,²¹]docosa-6,9,17,20-tetraen-5-yl 3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H38N2O9S2 (646.2018618000001)
(4r,5r,8r,9s)-9-formyl-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
2-(4,6-dimethyloct-6-en-2-yl)-6-oxooxan-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
2-hydroxy-n-[(4e)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}docos-4-en-2-yl]hexadecanimidic acid
(3s,4r,5e,9s,12ar,16as)-4-hydroxy-3,9,13-trimethyl-3,4,9,10,11,12a,16,16a-octahydro-2,8-benzodioxacyclotetradecine-1,7,12,15-tetrone
3-[(4s,7s,10s,13r)-17-(dodecan-2-yl)-6,9,12,15,16-pentahydroxy-13-(hydroxymethyl)-10-(1h-indol-3-ylmethyl)-2-oxo-4-phenyl-1-oxa-5,8,11,14-tetraazacycloheptadeca-5,8,11,14-tetraen-7-yl]propanimidic acid
C43H60N6O9 (804.4421550000001)
(3s,4s)-6-[(1e)-2-[(1r,3s,4s)-4-hydroxy-1,3-dimethylcyclohexyl]ethenyl]-3-methoxy-4-phenyl-3h-quinoline-2,4,5-triol
(1s,4s,5r,6s)-6-hydroxy-6-[(1r)-1-hydroxy-3-methylbut-2-en-1-yl]-5-methyl-8-methylidenebicyclo[2.2.2]octan-2-one
(3s)-3,6,8-trihydroxy-3-methyl-4h-2-benzopyran-1-one
n-[(2s)-4-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)-3-oxobutan-2-yl]carboximidic acid
C20H23NO5 (357.15761480000003)
(1r,4s,5s,11r,14s,15s)-5,15-dihydroxy-1,11-bis(methylsulfanyl)-3,13-diazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-6,8,16,18-tetraene-2,12-dione
7-[(4,5-dihydroxyhex-2-enoyl)oxy]-4-oxo-2-{6,16,24-trihydroxy-5,11,19,25-tetramethyl-3,9,14,21,27,28-hexaoxo-4,10,20,26-tetraoxatricyclo[14.11.1.0²,¹⁵]octacosa-7,22-dien-1-yl}octanoic acid
2-({[4-(acetyloxy)-3-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(5s)-5-[(7s,8e,13r)-7,13-dihydroxytetradec-8-en-1-yl]oxolan-2-one
1-(4-hydroxy-3,5-dimethoxyphenyl)-1,8-dimethoxynaphthalen-2-one
(2s,3s)-n-[(3s,6s,12s,15r,20as)-15-benzyl-3,6-bis[(2s)-butan-2-yl]-1,4,7,13-tetrahydroxy-16-oxo-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylpentanimidic acid
6-hydroxy-2,3-dimethyl-3,10a-bis(methylsulfanyl)-5ah,6h,10h-pyrazino[1,2-a]indole-1,4-dione
(3s,6r,9s,12r,15s,18r)-3,6,12,18-tetraisopropyl-4,10,16-trimethyl-9,15-bis(2-methylpropyl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
(2r,3r)-2-[(2s,4r)-5-[(2r,3r)-2,3-dimethyloxiran-2-yl]-4-methylpentan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(3e)-1-[(2e)-5-butyl-4-hydroxy-5h-1,3-oxazol-2-ylidene]-4-methyldec-3-en-2-one
2,15'-dihydroxy-16',16'-dimethyl-14'-oxa-2',10'-diazaspiro[indole-3,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-9',17'-dione
C23H19N3O5 (417.13246440000006)
5-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-18-oxa-3,13-diazapentacyclo[11.8.0.0³,¹¹.0⁴,⁹.0¹⁴,²⁰]henicosa-4,6,8,16,19-pentaen-15-yl 3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
C31H36N2O8S2 (628.1912976000001)
(3s,11'r,15'r)-2,15'-dihydroxy-16',16'-dimethyl-14'-oxa-2',10'-diazaspiro[indole-3,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-9',17'-dione
C23H19N3O5 (417.13246440000006)
(5-{[(2s,5r)-5-(furan-3-yl)-2-methyloxolan-2-yl]methyl}furan-3-yl)methanol
2-(7-hydroxy-4-methyl-6-methylideneoctan-2-yl)-6-oxo-2,3-dihydropyran-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(2s,3s)-3-{[(1s)-1-[(4-aminobutyl)-c-hydroxycarbonimidoyl]-2-phenylethyl]-c-hydroxycarbonimidoyl}oxirane-2-carboxylic acid
C17H23N3O5 (349.16376280000003)
(3r)-6-hydroxy-3-methyl-3-(4-methylpentyl)-2-benzofuran-1-one
n-[1-(4-methoxyphenyl)-3-oxo-4-(3,4,5-trimethoxyphenyl)butan-2-yl]carboximidic acid
1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
9-formyl-2-[({3-hydroxy-5-methoxy-6-methyl-4-[(2-methylhexa-2,4-dienoyl)oxy]oxan-2-yl}oxy)methyl]-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
2-(4,6-dimethyloct-6-en-2-yl)-6-oxo-2,3-dihydropyran-3-yl 8-(acetyloxy)-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
(3r,5as,6s,10ar)-6-hydroxy-2,3-dimethyl-3,10a-bis(methylsulfanyl)-5ah,6h,10h-pyrazino[1,2-a]indole-1,4-dione
6-hydroxy-6-(1-hydroxy-3-methylbut-2-en-1-yl)-5-methyl-8-methylidenebicyclo[2.2.2]octan-2-one
(1s,2r,4r)-2',8-dihydroxy-4,5-dimethyl-3-thia-5,7-diazaspiro[bicyclo[2.2.2]octane-2,3'-indol]-7-en-6-one
C14H13N3O3S (303.06775880000004)
(5r,6r)-5-(chloromethyl)-5-hydroxy-6-(hydroxymethyl)-6-[(2s,3r)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]oxan-2-one
(1r,2s,4r,5r,8r,9s,11s)-9-formyl-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4z)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
2-(4,6-dimethyl-8-oxooct-6-en-2-yl)-6-oxo-2,3-dihydropyran-3-yl 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
15'-hydroxy-2,16',16'-trimethyl-2,9a-dihydro-1h-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
(4z)-1-(furan-3-yl)-4,8-dimethylnona-4,7-diene-1,6-dione
(5s,7r)-3-{[(2s,3r,8r,10r)-3-hydroxy-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-2-yl](methyl)amino}-7-[(2s)-7-methyl-3-oxooct-6-en-2-yl]-8-methylidene-1-oxaspiro[4.5]dec-3-en-2-one
(2r,7s)-7-{[(2e,4r,5s)-4,5-dihydroxyhex-2-enoyl]oxy}-4-oxo-2-[(1s,2s,5s,6r,7e,11s,15s,16s,19s,22e,24r,25s)-6,16,24-trihydroxy-5,11,19,25-tetramethyl-3,9,14,21,27,28-hexaoxo-4,10,20,26-tetraoxatricyclo[14.11.1.0²,¹⁵]octacosa-7,22-dien-1-yl]octanoic acid
(3s)-6,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one
(2r,3r)-2-[(2s,4r,7s)-7-hydroxy-4-methyl-6-methylideneoctan-2-yl]-6-oxo-2,3-dihydropyran-3-yl (2e,4e,6s)-8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
1-(furan-3-yl)-4,9-dihydroxy-4,8-dimethylnonane-1,6-dione
(2s,3s)-n-[(3s,6s,12s,15r,20as)-15-benzyl-3-[(2s)-butan-2-yl]-1,4,7,13-tetrahydroxy-6-isopropyl-16-oxo-3h,6h,9h,10h,11h,12h,15h,18h,19h,20h,20ah-pyrrolo[1,2-d]1,4,7,10,13-pentaazacyclooctadecan-12-yl]-2-[(1-hydroxyethylidene)amino]-3-methylpentanimidic acid
C38H59N7O7 (725.4475744000001)
8-hydroxy-3-(hydroxymethyl)-6-methoxyisochromen-1-one
1-(furan-3-yl)-4',5-dimethyl-2,8-dioxaspiro[bicyclo[3.2.1]octane-3,2'-oxolane]
16-[(3-hydroxyoctanoyl)oxy]-2,13-dioxo-8,19-dioxa-23,24-dithia-3,14-diazahexacyclo[10.10.2.0¹,¹⁴.0³,¹².0⁴,¹⁰.0¹⁵,²¹]tetracosa-6,9,17,20-tetraen-5-yl 3-hydroxyoctanoate
(1r,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-4-(acetyloxy)-3-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid
(1r,4s,5s,11r,14s,15s)-15-hydroxy-1,11-bis(methylsulfanyl)-2,12-dioxo-3,13-diazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-6,8,16,18-tetraen-5-yl (2r,3s,4s)-3-hydroxy-2,4,6-trimethyl-5-oxooct-6-enoate
(9s,9ar,11's,15's)-15'-hydroxy-2,2,16',16'-tetramethyl-1,9a-dihydro-14'-oxa-2',10'-diazaspiro[imidazo[1,2-a]indole-9,13'-tetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadecane]-1',3',5',7'-tetraene-3,9',17'-trione
C27H26N4O5 (486.19031060000003)